Hydrochloric Acid → rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

HRID 988844Notes

Reaction equation

HRID 988844 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C-:10]#[N:11].[Na+].[S:13]1[C:21]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]=2[CH:15]=[CH:14]1.Cl.[NH4+].[OH-]>CO.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([N:18]1[CH2:19][CH2:20][C:21]2[S:13][CH:14]=[CH:15][C:16]=2[CH2:17]1)[C:10]#[N:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 69962-ChlorobenzaldehydeHCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

Product 1

HCID 11369741rac-2-(2-Chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
31 °C

Procedure

123.83 g (880 mmol) o-chlorobenzaldehyde and 44 g (897 mmol) sodium cyanide were added to in 100 mL of methanol and water (1:1) mixture. To this 150 g (1070 mmol) 6,7-dihydro-4H-thieno[3,2-c]pyridine was added, followed by the addition of 10 mL concentrated hydrochloric acid and was stirred for 2 days at 31° C. temperature. The pH of reaction mixture was adjusted to 7.5-8.0 using NH4OH. The product was extracted with ethyl acetate (2×50 mL) and washed with water (2×50 mL), brine (50 mL) and was dried over sodium sulfate, and isolated as given in Example 1. The amount of white solid product obtained was 33 g (13%), which was characterized as usual.

Workup

  1. customThe pH of reaction mixture
  2. extractionThe product was extracted with ethyl acetate (2×50 mL)
  3. washwashed with water (2×50 mL), brine (50 mL)
  4. dry with materialwas dried over sodium sulfate
  5. customisolated
  6. customThe amount of white solid product obtained

Sources & evidence

ORD record
ord-34290a74c2ee41c689d84f377d9399bb
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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